While prominent in the 1970s for his recordings "Spiders & Snakes", "Swamp Witch", "Under the Scotsman's Kilt", "My Girl Bill", and "Wildwood Weed",[2] Stafford headlined at his own theater in Branson, Missouri, from 1990 to 2020.

In high school, he played in a band called the Legends, along with friends Bobby Braddock, Kent LaVoie (also known as Lobo) and Gram Parsons (of the Byrds and The Flying Burrito Brothers).

The Jim Stafford Show was a six-week summer variety series shown on ABC from July 30, 1975 (1975-07-30) to September 3, 1975 (1975-09-03).

It featured Valerie Curtin, Richard Stahl, Deborah Allen, Cyndi Wood, and Gallagher, and was co-produced by Tony Scotti.

Stafford was credited with being the supervising writer for The Smothers Brothers Comedy Hour revival show, which aired on CBS in 1988.

[4] The famous "guitar neck" in front of the theater, regarded as a beloved Branson landmark, was saved in an effort by preservationists and fans.